Flights from Chicago to Calgary (ORD to YYC)

Discover more affordable routes and cheaper dates from Chicago to Calgary (ORD to YYC) within a date range.

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US$268

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

6:15am - 10:25pm
Tue Jul 8th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 6 nights

Tue Jul 8th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Tue Jul 8th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$268

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

6:15am - 10:25pm
Wed Jul 16th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 14 nights

Wed Jul 16th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Wed Jul 16th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$274

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

6:15am - 6:06pm
Fri Jul 4th 2025

10h 51m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 2 nights

Fri Jul 4th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 5h 51m

Fri Jul 4th 2025 United Airlines · UA 1819 Depart at 2:40pm from Denver (DEN) Fly for 2h 26m Arrive at 6:06pm in Chicago (ORD)
US$274

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

6:15am - 9:13pm
Fri Jul 4th 2025

13h 58m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 2 nights

Fri Jul 4th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 8h 53m

Fri Jul 4th 2025 United Airlines · UA 1898 Depart at 5:42pm from Denver (DEN) Fly for 2h 31m Arrive at 9:13pm in Chicago (ORD)
US$274

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

6:15am - 10:25pm
Fri Jul 4th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 2 nights

Fri Jul 4th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Fri Jul 4th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$274

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

6:15am - 11:57pm
Fri Jul 4th 2025

16h 42m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 2 nights

Fri Jul 4th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 11h 45m

Fri Jul 4th 2025 United Airlines · UA 377 Depart at 8:34pm from Denver (DEN) Fly for 2h 23m Arrive at 11:57pm in Chicago (ORD)
US$299

4:00pm - 1:05am
Sat Jul 12th 2025

10h 5m
Chicago (ORD) → Calgary (YYC)

1 Stop

1:05am - 9:54am
Tue Jul 15th 2025

7h 49m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sat Jul 12th 2025 Air Canada · AC 508 Depart at 4:00pm from Chicago (ORD) Fly for 1h 45m Arrive at 6:45pm in Toronto (YYZ)

Layover in Toronto for 4h 5m

Sat Jul 12th 2025 Air Canada · AC 159 Depart at 10:50pm from Toronto (YYZ) Fly for 4h 15m Arrive at 1:05am in Calgary (YYC)

Stay in Calgary for 2 nights

Tue Jul 15th 2025 Air Canada · AC 316 Depart at 1:05am from Calgary (YYC) Fly for 4h 5m Arrive at 7:10am in Montreal (YUL)

Layover in Montreal for 1h 10m

Tue Jul 15th 2025 Air Canada · AC 521 Depart at 8:20am from Montreal (YUL) Fly for 2h 34m Arrive at 9:54am in Chicago (ORD)
US$299

8:25pm - 8:45am
Sat Jul 12th 2025

13h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

1:05am - 9:54am
Tue Jul 15th 2025

7h 49m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sat Jul 12th 2025 Air Canada · AC 510 Depart at 8:25pm from Chicago (ORD) Fly for 1h 45m Arrive at 11:10pm in Toronto (YYZ)

Layover in Toronto for 7h 20m

Sun Jul 13th 2025 Air Canada · AC 131 Depart at 6:30am from Toronto (YYZ) Fly for 4h 15m Arrive at 8:45am in Calgary (YYC)

Stay in Calgary for 1 night

Tue Jul 15th 2025 Air Canada · AC 316 Depart at 1:05am from Calgary (YYC) Fly for 4h 5m Arrive at 7:10am in Montreal (YUL)

Layover in Montreal for 1h 10m

Tue Jul 15th 2025 Air Canada · AC 521 Depart at 8:20am from Montreal (YUL) Fly for 2h 34m Arrive at 9:54am in Chicago (ORD)
US$302

10:40am - 11:03pm
Sat Jul 12th 2025

13h 23m
Chicago (ORD) → Calgary (YYC)

1 Stop

1:05am - 9:54am
Tue Jul 15th 2025

7h 49m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sat Jul 12th 2025 Air Canada · AC 522 Depart at 10:40am from Chicago (ORD) Fly for 2h 19m Arrive at 1:59pm in Montreal (YUL)

Layover in Montreal for 6h 31m

Sat Jul 12th 2025 Air Canada · AC 327 Depart at 8:30pm from Montreal (YUL) Fly for 4h 33m Arrive at 11:03pm in Calgary (YYC)

Stay in Calgary for 2 nights

Tue Jul 15th 2025 Air Canada · AC 316 Depart at 1:05am from Calgary (YYC) Fly for 4h 5m Arrive at 7:10am in Montreal (YUL)

Layover in Montreal for 1h 10m

Tue Jul 15th 2025 Air Canada · AC 521 Depart at 8:20am from Montreal (YUL) Fly for 2h 34m Arrive at 9:54am in Chicago (ORD)
US$306

4:00pm - 1:05am
Sat Jul 12th 2025

10h 5m
Chicago (ORD) → Calgary (YYC)

1 Stop

6:00am - 2:54pm
Tue Jul 15th 2025

7h 54m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sat Jul 12th 2025 Air Canada · AC 508 Depart at 4:00pm from Chicago (ORD) Fly for 1h 45m Arrive at 6:45pm in Toronto (YYZ)

Layover in Toronto for 4h 5m

Sat Jul 12th 2025 Air Canada · AC 159 Depart at 10:50pm from Toronto (YYZ) Fly for 4h 15m Arrive at 1:05am in Calgary (YYC)

Stay in Calgary for 2 nights

Tue Jul 15th 2025 Air Canada · AC 130 Depart at 6:00am from Calgary (YYC) Fly for 3h 49m Arrive at 11:49am in Toronto (YYZ)

Layover in Toronto for 2h 11m

Tue Jul 15th 2025 Air Canada · AC 507 Depart at 2:00pm from Toronto (YYZ) Fly for 1h 54m Arrive at 2:54pm in Chicago (ORD)
US$306

4:00pm - 1:05am
Wed Jul 9th 2025

10h 5m
Chicago (ORD) → Calgary (YYC)

1 Stop

6:00am - 2:54pm
Wed Jul 16th 2025

7h 54m
Calgary (YYC) → Chicago (ORD)

1 Stop

Wed Jul 9th 2025 Air Canada · AC 508 Depart at 4:00pm from Chicago (ORD) Fly for 1h 45m Arrive at 6:45pm in Toronto (YYZ)

Layover in Toronto for 4h 5m

Wed Jul 9th 2025 Air Canada · AC 159 Depart at 10:50pm from Toronto (YYZ) Fly for 4h 15m Arrive at 1:05am in Calgary (YYC)

Stay in Calgary for 6 nights

Wed Jul 16th 2025 Air Canada · AC 130 Depart at 6:00am from Calgary (YYC) Fly for 3h 49m Arrive at 11:49am in Toronto (YYZ)

Layover in Toronto for 2h 11m

Wed Jul 16th 2025 Air Canada · AC 507 Depart at 2:00pm from Toronto (YYZ) Fly for 1h 54m Arrive at 2:54pm in Chicago (ORD)
US$306

8:25pm - 8:45am
Sat Jul 12th 2025

13h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

6:00am - 2:54pm
Tue Jul 15th 2025

7h 54m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sat Jul 12th 2025 Air Canada · AC 510 Depart at 8:25pm from Chicago (ORD) Fly for 1h 45m Arrive at 11:10pm in Toronto (YYZ)

Layover in Toronto for 7h 20m

Sun Jul 13th 2025 Air Canada · AC 131 Depart at 6:30am from Toronto (YYZ) Fly for 4h 15m Arrive at 8:45am in Calgary (YYC)

Stay in Calgary for 1 night

Tue Jul 15th 2025 Air Canada · AC 130 Depart at 6:00am from Calgary (YYC) Fly for 3h 49m Arrive at 11:49am in Toronto (YYZ)

Layover in Toronto for 2h 11m

Tue Jul 15th 2025 Air Canada · AC 507 Depart at 2:00pm from Toronto (YYZ) Fly for 1h 54m Arrive at 2:54pm in Chicago (ORD)
US$309

10:40am - 11:03pm
Sat Jul 12th 2025

13h 23m
Chicago (ORD) → Calgary (YYC)

1 Stop

6:00am - 2:54pm
Tue Jul 15th 2025

7h 54m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sat Jul 12th 2025 Air Canada · AC 522 Depart at 10:40am from Chicago (ORD) Fly for 2h 19m Arrive at 1:59pm in Montreal (YUL)

Layover in Montreal for 6h 31m

Sat Jul 12th 2025 Air Canada · AC 327 Depart at 8:30pm from Montreal (YUL) Fly for 4h 33m Arrive at 11:03pm in Calgary (YYC)

Stay in Calgary for 2 nights

Tue Jul 15th 2025 Air Canada · AC 130 Depart at 6:00am from Calgary (YYC) Fly for 3h 49m Arrive at 11:49am in Toronto (YYZ)

Layover in Toronto for 2h 11m

Tue Jul 15th 2025 Air Canada · AC 507 Depart at 2:00pm from Toronto (YYZ) Fly for 1h 54m Arrive at 2:54pm in Chicago (ORD)
US$321

5:30pm - 8:19pm
Tue Jul 8th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 11th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 8th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 2 nights

Fri Jul 11th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$321

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sat Jul 12th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 9 nights

Sat Jul 12th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$321

5:30pm - 8:19pm
Tue Jul 8th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sat Jul 12th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 8th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 3 nights

Sat Jul 12th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$321

5:30pm - 8:19pm
Wed Jul 9th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 11th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 9th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 1 night

Fri Jul 11th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$321

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 11th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 8 nights

Fri Jul 11th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$321

5:30pm - 8:19pm
Fri Jul 11th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sat Jul 12th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Fri Jul 11th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 0 nights

Sat Jul 12th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$321

5:30pm - 8:19pm
Wed Jul 9th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sat Jul 12th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 9th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 2 nights

Sat Jul 12th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$330

4:00pm - 1:05am
Sat Jul 12th 2025

10h 5m
Chicago (ORD) → Calgary (YYC)

1 Stop

7:00pm - 9:09am
Tue Jul 15th 2025

13h 9m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sat Jul 12th 2025 Air Canada · AC 508 Depart at 4:00pm from Chicago (ORD) Fly for 1h 45m Arrive at 6:45pm in Toronto (YYZ)

Layover in Toronto for 4h 5m

Sat Jul 12th 2025 Air Canada · AC 159 Depart at 10:50pm from Toronto (YYZ) Fly for 4h 15m Arrive at 1:05am in Calgary (YYC)

Stay in Calgary for 2 nights

Tue Jul 15th 2025 Air Canada · AC 158 Depart at 7:00pm from Calgary (YYC) Fly for 3h 49m Arrive at 12:49am in Toronto (YYZ)

Layover in Toronto for 7h 26m

Wed Jul 16th 2025 Air Canada · AC 503 Depart at 8:15am from Toronto (YYZ) Fly for 1h 54m Arrive at 9:09am in Chicago (ORD)
US$330

8:25pm - 8:45am
Sat Jul 12th 2025

13h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

7:00pm - 9:09am
Tue Jul 15th 2025

13h 9m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sat Jul 12th 2025 Air Canada · AC 510 Depart at 8:25pm from Chicago (ORD) Fly for 1h 45m Arrive at 11:10pm in Toronto (YYZ)

Layover in Toronto for 7h 20m

Sun Jul 13th 2025 Air Canada · AC 131 Depart at 6:30am from Toronto (YYZ) Fly for 4h 15m Arrive at 8:45am in Calgary (YYC)

Stay in Calgary for 2 nights

Tue Jul 15th 2025 Air Canada · AC 158 Depart at 7:00pm from Calgary (YYC) Fly for 3h 49m Arrive at 12:49am in Toronto (YYZ)

Layover in Toronto for 7h 26m

Wed Jul 16th 2025 Air Canada · AC 503 Depart at 8:15am from Toronto (YYZ) Fly for 1h 54m Arrive at 9:09am in Chicago (ORD)
US$333

10:40am - 11:03pm
Sat Jul 12th 2025

13h 23m
Chicago (ORD) → Calgary (YYC)

1 Stop

7:00pm - 9:09am
Tue Jul 15th 2025

13h 9m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sat Jul 12th 2025 Air Canada · AC 522 Depart at 10:40am from Chicago (ORD) Fly for 2h 19m Arrive at 1:59pm in Montreal (YUL)

Layover in Montreal for 6h 31m

Sat Jul 12th 2025 Air Canada · AC 327 Depart at 8:30pm from Montreal (YUL) Fly for 4h 33m Arrive at 11:03pm in Calgary (YYC)

Stay in Calgary for 2 nights

Tue Jul 15th 2025 Air Canada · AC 158 Depart at 7:00pm from Calgary (YYC) Fly for 3h 49m Arrive at 12:49am in Toronto (YYZ)

Layover in Toronto for 7h 26m

Wed Jul 16th 2025 Air Canada · AC 503 Depart at 8:15am from Toronto (YYZ) Fly for 1h 54m Arrive at 9:09am in Chicago (ORD)
US$348

5:30pm - 8:19pm
Tue Jul 1st 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 11th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 1st 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 9 nights

Fri Jul 11th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$348

5:30pm - 8:19pm
Tue Jul 1st 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sat Jul 12th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 1st 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 10 nights

Sat Jul 12th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$389

5:30pm - 8:19pm
Sat Jul 5th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sat Jul 12th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Sat Jul 5th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 6 nights

Sat Jul 12th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$408

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Mon Jul 14th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 11 nights

Mon Jul 14th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$408

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Tue Jul 15th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 12 nights

Tue Jul 15th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$408

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Thu Jul 3rd 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 0 nights

Thu Jul 3rd 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$408

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Tue Jul 8th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 5 nights

Tue Jul 8th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$408

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Wed Jul 9th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 6 nights

Wed Jul 9th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$408

5:30pm - 8:19pm
Tue Jul 8th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Wed Jul 9th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 8th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 0 nights

Wed Jul 9th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$408

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Wed Jul 16th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 13 nights

Wed Jul 16th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$408

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 18th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 15 nights

Fri Jul 18th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$408

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Thu Jul 17th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 14 nights

Thu Jul 17th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$452

5:30pm - 8:19pm
Thu Jul 3rd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sat Jul 12th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Thu Jul 3rd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 8 nights

Sat Jul 12th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$464

5:30pm - 8:19pm
Mon Jul 7th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 11th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Mon Jul 7th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 3 nights

Fri Jul 11th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$465

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sun Jul 6th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 3 nights

Sun Jul 6th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$471

5:30pm - 8:19pm
Tue Jul 8th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Mon Jul 14th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 8th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 5 nights

Mon Jul 14th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$481

5:30pm - 8:19pm
Fri Jul 4th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sat Jul 12th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Fri Jul 4th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 7 nights

Sat Jul 12th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$487

5:30pm - 8:19pm
Sat Jul 12th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Tue Jul 15th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Sat Jul 12th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 2 nights

Tue Jul 15th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$487

5:30pm - 8:19pm
Fri Jul 11th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 18th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Fri Jul 11th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 6 nights

Fri Jul 18th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$487

5:30pm - 8:19pm
Fri Jul 11th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Thu Jul 17th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Fri Jul 11th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 5 nights

Thu Jul 17th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$489

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

8:30am - 12:49pm
Wed Jul 9th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 7 nights

Wed Jul 9th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$489

5:00am - 6:20pm
Sun Jul 6th 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

8:30am - 12:49pm
Wed Jul 9th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Sun Jul 6th 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Sun Jul 6th 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 2 nights

Wed Jul 9th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$489

5:00am - 6:20pm
Sun Jul 6th 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

8:30am - 12:49pm
Thu Jul 10th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Sun Jul 6th 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Sun Jul 6th 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 3 nights

Thu Jul 10th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$489

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

8:30am - 12:49pm
Wed Jul 16th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 14 nights

Wed Jul 16th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$489

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

8:30am - 12:49pm
Tue Jul 15th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 13 nights

Tue Jul 15th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$489

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

12:30pm - 4:50pm
Wed Jul 16th 2025

3h 20m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 14 nights

Wed Jul 16th 2025 United Airlines · UA 1655 Depart at 12:30pm from Calgary (YYC) Fly for 3h 20m Arrive at 4:50pm in Chicago (ORD)
US$495

7:45pm - 10:29pm
Sat Jul 5th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Wed Jul 16th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sat Jul 5th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 10 nights

Wed Jul 16th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Wed Jul 16th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$495

7:45pm - 10:29pm
Wed Jul 9th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Wed Jul 16th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Wed Jul 9th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 6 nights

Wed Jul 16th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Wed Jul 16th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$495

7:45pm - 10:29pm
Mon Jul 7th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Wed Jul 16th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Mon Jul 7th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 8 nights

Wed Jul 16th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Wed Jul 16th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$495

7:45pm - 10:29pm
Sun Jul 13th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Wed Jul 16th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sun Jul 13th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 2 nights

Wed Jul 16th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Wed Jul 16th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$495

7:45pm - 10:29pm
Tue Jul 1st 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Tue Jul 8th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 6 nights

Tue Jul 8th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Tue Jul 8th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$495

7:45pm - 10:29pm
Sun Jul 6th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Tue Jul 8th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sun Jul 6th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 1 night

Tue Jul 8th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Tue Jul 8th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$495

7:45pm - 10:29pm
Tue Jul 1st 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Wed Jul 16th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 14 nights

Wed Jul 16th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Wed Jul 16th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$495

7:45pm - 10:29pm
Fri Jul 4th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Tue Jul 8th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Fri Jul 4th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 3 nights

Tue Jul 8th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Tue Jul 8th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$495

9:00am - 11:54am
Tue Jul 1st 2025

3h 54m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Tue Jul 8th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 764 Depart at 9:00am from Chicago (ORD) Fly for 3h 54m Arrive at 11:54am in Calgary (YYC)

Stay in Calgary for 6 nights

Tue Jul 8th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Tue Jul 8th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$495

9:00am - 11:54am
Tue Jul 1st 2025

3h 54m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Wed Jul 16th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 764 Depart at 9:00am from Chicago (ORD) Fly for 3h 54m Arrive at 11:54am in Calgary (YYC)

Stay in Calgary for 14 nights

Wed Jul 16th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Wed Jul 16th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$496

5:30pm - 8:19pm
Wed Jul 9th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Mon Jul 14th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 9th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 4 nights

Mon Jul 14th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$496

5:30pm - 8:19pm
Wed Jul 9th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Wed Jul 16th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 9th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 6 nights

Wed Jul 16th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$496

5:30pm - 8:19pm
Fri Jul 11th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Tue Jul 15th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Fri Jul 11th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 3 nights

Tue Jul 15th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$499

5:30pm - 8:19pm
Sat Jul 5th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Tue Jul 15th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Sat Jul 5th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 9 nights

Tue Jul 15th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$499

5:30pm - 8:19pm
Tue Jul 1st 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 18th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 1st 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 16 nights

Fri Jul 18th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$505

3:40pm - 11:03pm
Mon Jul 7th 2025

8h 23m
Chicago (ORD) → Calgary (YYC)

1 Stop

1:05am - 9:54am
Wed Jul 9th 2025

7h 49m
Calgary (YYC) → Chicago (ORD)

1 Stop

Mon Jul 7th 2025 Air Canada · AC 8964 Depart at 3:40pm from Chicago (ORD) Fly for 2h 18m Arrive at 6:58pm in Montreal (YUL)

Layover in Montreal for 1h 32m

Mon Jul 7th 2025 Air Canada · AC 327 Depart at 8:30pm from Montreal (YUL) Fly for 4h 33m Arrive at 11:03pm in Calgary (YYC)

Stay in Calgary for 1 night

Wed Jul 9th 2025 Air Canada · AC 316 Depart at 1:05am from Calgary (YYC) Fly for 4h 5m Arrive at 7:10am in Montreal (YUL)

Layover in Montreal for 1h 10m

Wed Jul 9th 2025 Air Canada · AC 521 Depart at 8:20am from Montreal (YUL) Fly for 2h 34m Arrive at 9:54am in Chicago (ORD)
US$505

5:00am - 6:20pm
Sun Jul 6th 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

1:30pm - 10:25pm
Sat Jul 12th 2025

7h 55m
Calgary (YYC) → Chicago (ORD)

1 Stop

Sun Jul 6th 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Sun Jul 6th 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 5 nights

Sat Jul 12th 2025 United Airlines · UA 1953 Depart at 1:30pm from Calgary (YYC) Fly for 2h 34m Arrive at 4:04pm in Denver (DEN)

Layover in Denver for 2h 56m

Sat Jul 12th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$510

5:30pm - 8:19pm
Sun Jul 6th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 11th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Sun Jul 6th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 4 nights

Fri Jul 11th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$525

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:30am - 10:02am
Sat Jul 12th 2025

8h 32m
Calgary (YYC) → Chicago (ORD)

1 Stop

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 9 nights

Sat Jul 12th 2025 WestJet · WS 1992 Depart at 12:30am from Calgary (YYC) Fly for 4h 24m Arrive at 6:54am in Atlanta (ATL)

Layover in Atlanta for 2h 1m

Sat Jul 12th 2025 WestJet · WS 6879 Depart at 8:55am from Atlanta (ATL) Fly for 2h 7m Arrive at 10:02am in Chicago (ORD)
US$539

10:40am - 11:03pm
Tue Jul 1st 2025

13h 23m
Chicago (ORD) → Calgary (YYC)

1 Stop

1:05am - 9:54am
Sun Jul 6th 2025

7h 49m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 Air Canada · AC 522 Depart at 10:40am from Chicago (ORD) Fly for 2h 19m Arrive at 1:59pm in Montreal (YUL)

Layover in Montreal for 6h 31m

Tue Jul 1st 2025 Air Canada · AC 327 Depart at 8:30pm from Montreal (YUL) Fly for 4h 33m Arrive at 11:03pm in Calgary (YYC)

Stay in Calgary for 4 nights

Sun Jul 6th 2025 Air Canada · AC 316 Depart at 1:05am from Calgary (YYC) Fly for 4h 5m Arrive at 7:10am in Montreal (YUL)

Layover in Montreal for 1h 10m

Sun Jul 6th 2025 Air Canada · AC 521 Depart at 8:20am from Montreal (YUL) Fly for 2h 34m Arrive at 9:54am in Chicago (ORD)
US$540

5:00am - 6:20pm
Sun Jul 6th 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

8:30am - 12:49pm
Fri Jul 11th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Sun Jul 6th 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Sun Jul 6th 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 4 nights

Fri Jul 11th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$540

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

8:30am - 12:49pm
Fri Jul 11th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 9 nights

Fri Jul 11th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$543

4:00pm - 1:05am
Wed Jul 9th 2025

10h 5m
Chicago (ORD) → Calgary (YYC)

1 Stop

11:55pm - 9:09am
Sat Jul 12th 2025

8h 14m
Calgary (YYC) → Chicago (ORD)

1 Stop

Wed Jul 9th 2025 Air Canada · AC 508 Depart at 4:00pm from Chicago (ORD) Fly for 1h 45m Arrive at 6:45pm in Toronto (YYZ)

Layover in Toronto for 4h 5m

Wed Jul 9th 2025 Air Canada · AC 159 Depart at 10:50pm from Toronto (YYZ) Fly for 4h 15m Arrive at 1:05am in Calgary (YYC)

Stay in Calgary for 2 nights

Sat Jul 12th 2025 Air Canada · AC 154 Depart at 11:55pm from Calgary (YYC) Fly for 3h 49m Arrive at 5:44am in Toronto (YYZ)

Layover in Toronto for 2h 31m

Sun Jul 13th 2025 Air Canada · AC 503 Depart at 8:15am from Toronto (YYZ) Fly for 1h 54m Arrive at 9:09am in Chicago (ORD)
US$546

7:45pm - 10:29pm
Wed Jul 2nd 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Wed Jul 16th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Wed Jul 2nd 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 13 nights

Wed Jul 16th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Wed Jul 16th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$546

7:45pm - 10:29pm
Thu Jul 3rd 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

6:15am - 10:25pm
Tue Jul 8th 2025

15h 10m
Calgary (YYC) → Chicago (ORD)

1 Stop

Thu Jul 3rd 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 4 nights

Tue Jul 8th 2025 United Airlines · UA 550 Depart at 6:15am from Calgary (YYC) Fly for 2h 34m Arrive at 8:49am in Denver (DEN)

Layover in Denver for 10h 11m

Tue Jul 8th 2025 United Airlines · UA 2258 Depart at 7:00pm from Denver (DEN) Fly for 2h 25m Arrive at 10:25pm in Chicago (ORD)
US$557

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

9:15am - 4:34pm
Sat Jul 12th 2025

6h 19m
Calgary (YYC) → Chicago (ORD)

1 Stop

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 9 nights

Sat Jul 12th 2025 WestJet · WS 1578 Depart at 9:15am from Calgary (YYC) Fly for 3h 43m Arrive at 2:58pm in Detroit (DTW)

Layover in Detroit for 1h 12m

Sat Jul 12th 2025 WestJet · WS 7421 Depart at 4:10pm from Detroit (DTW) Fly for 1h 24m Arrive at 4:34pm in Chicago (ORD)
US$557

8:40am - 3:52pm
Wed Jul 9th 2025

8h 12m
Chicago (ORD) → Calgary (YYC)

1 Stop

1:05am - 9:54am
Wed Jul 16th 2025

7h 49m
Calgary (YYC) → Chicago (ORD)

1 Stop

Wed Jul 9th 2025 Air Canada · AC 8958 Depart at 8:40am from Chicago (ORD) Fly for 2h 18m Arrive at 11:58am in Montreal (YUL)

Layover in Montreal for 1h 32m

Wed Jul 9th 2025 Air Canada · AC 323 Depart at 1:30pm from Montreal (YUL) Fly for 4h 22m Arrive at 3:52pm in Calgary (YYC)

Stay in Calgary for 6 nights

Wed Jul 16th 2025 Air Canada · AC 316 Depart at 1:05am from Calgary (YYC) Fly for 4h 5m Arrive at 7:10am in Montreal (YUL)

Layover in Montreal for 1h 10m

Wed Jul 16th 2025 Air Canada · AC 521 Depart at 8:20am from Montreal (YUL) Fly for 2h 34m Arrive at 9:54am in Chicago (ORD)
US$561

5:30pm - 8:19pm
Mon Jul 7th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Tue Jul 15th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Mon Jul 7th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 7 nights

Tue Jul 15th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$561

5:30pm - 8:19pm
Sun Jul 13th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 18th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Sun Jul 13th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 4 nights

Fri Jul 18th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$562

5:00am - 6:20pm
Tue Jul 1st 2025

14h 20m
Chicago (ORD) → Calgary (YYC)

1 Stop

1:30pm - 9:13pm
Sat Jul 5th 2025

6h 43m
Calgary (YYC) → Chicago (ORD)

1 Stop

Tue Jul 1st 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)

Layover in Denver for 9h 13m

Tue Jul 1st 2025 United Airlines · UA 1225 Depart at 3:50pm from Denver (DEN) Fly for 2h 30m Arrive at 6:20pm in Calgary (YYC)

Stay in Calgary for 3 nights

Sat Jul 5th 2025 United Airlines · UA 1953 Depart at 1:30pm from Calgary (YYC) Fly for 2h 34m Arrive at 4:04pm in Denver (DEN)

Layover in Denver for 1h 38m

Sat Jul 5th 2025 United Airlines · UA 1898 Depart at 5:42pm from Denver (DEN) Fly for 2h 31m Arrive at 9:13pm in Chicago (ORD)
US$578

5:30pm - 8:19pm
Thu Jul 10th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Mon Jul 14th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Thu Jul 10th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 3 nights

Mon Jul 14th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$578

5:30pm - 8:19pm
Thu Jul 3rd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Wed Jul 9th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Thu Jul 3rd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 5 nights

Wed Jul 9th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$578

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sat Jul 5th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 2 nights

Sat Jul 5th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$582

5:30pm - 8:19pm
Thu Jul 10th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Fri Jul 18th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Thu Jul 10th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 7 nights

Fri Jul 18th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$583

12:17pm - 4:48pm
Wed Jul 9th 2025

5h 31m
Chicago (ORD) → Calgary (YYC)

1 Stop

12:15pm - 4:44pm
Sat Jul 12th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Wed Jul 9th 2025 WestJet · WS 8232 Depart at 12:17pm from Chicago (ORD) Fly for 1h 33m Arrive at 1:50pm in Minneapolis (MSP)

Layover in Minneapolis for 1h 10m

Wed Jul 9th 2025 WestJet · WS 1611 Depart at 3:00pm from Minneapolis (MSP) Fly for 2h 48m Arrive at 4:48pm in Calgary (YYC)

Stay in Calgary for 2 nights

Sat Jul 12th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$589

5:30pm - 8:19pm
Fri Jul 4th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Wed Jul 9th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Fri Jul 4th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 4 nights

Wed Jul 9th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$598

5:30pm - 8:19pm
Wed Jul 2nd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

9:15am - 4:34pm
Mon Jul 7th 2025

6h 19m
Calgary (YYC) → Chicago (ORD)

1 Stop

Wed Jul 2nd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 4 nights

Mon Jul 7th 2025 WestJet · WS 1578 Depart at 9:15am from Calgary (YYC) Fly for 3h 43m Arrive at 2:58pm in Detroit (DTW)

Layover in Detroit for 1h 12m

Mon Jul 7th 2025 WestJet · WS 7421 Depart at 4:10pm from Detroit (DTW) Fly for 1h 24m Arrive at 4:34pm in Chicago (ORD)
US$607

5:30pm - 8:19pm
Fri Jul 4th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Tue Jul 8th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Fri Jul 4th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 3 nights

Tue Jul 8th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$608

5:30pm - 8:19pm
Sat Jul 5th 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Thu Jul 10th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Sat Jul 5th 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 4 nights

Thu Jul 10th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$635

5:30pm - 8:19pm
Tue Jul 1st 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Sun Jul 6th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 1st 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 4 nights

Sun Jul 6th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$651

5:30pm - 8:19pm
Thu Jul 3rd 2025

3h 49m
Chicago (ORD) → Calgary (YYC)

Direct

12:15pm - 4:44pm
Mon Jul 7th 2025

3h 29m
Calgary (YYC) → Chicago (ORD)

Direct

Thu Jul 3rd 2025 WestJet · WS 1589 Depart at 5:30pm from Chicago (ORD) Fly for 3h 49m Arrive at 8:19pm in Calgary (YYC)

Stay in Calgary for 3 nights

Mon Jul 7th 2025 WestJet · WS 1588 Depart at 12:15pm from Calgary (YYC) Fly for 3h 29m Arrive at 4:44pm in Chicago (ORD)
US$710

7:45pm - 10:29pm
Thu Jul 10th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

8:30am - 12:49pm
Wed Jul 16th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Thu Jul 10th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 5 nights

Wed Jul 16th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$710

7:45pm - 10:29pm
Fri Jul 4th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

8:30am - 12:49pm
Thu Jul 10th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Fri Jul 4th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 5 nights

Thu Jul 10th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$710

7:45pm - 10:29pm
Thu Jul 10th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

8:30am - 12:49pm
Fri Jul 18th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Thu Jul 10th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 7 nights

Fri Jul 18th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$710

7:45pm - 10:29pm
Sun Jul 13th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

8:30am - 12:49pm
Thu Jul 17th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Sun Jul 13th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 3 nights

Thu Jul 17th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$710

7:45pm - 10:29pm
Sun Jul 13th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

8:30am - 12:49pm
Fri Jul 18th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Sun Jul 13th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 4 nights

Fri Jul 18th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$710

7:45pm - 10:29pm
Mon Jul 7th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

8:30am - 12:49pm
Tue Jul 15th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Mon Jul 7th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 7 nights

Tue Jul 15th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$715

7:45pm - 10:29pm
Sat Jul 5th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

8:30am - 12:49pm
Wed Jul 9th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Sat Jul 5th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 3 nights

Wed Jul 9th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$715

7:45pm - 10:29pm
Sun Jul 6th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

8:30am - 12:49pm
Wed Jul 9th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Sun Jul 6th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 2 nights

Wed Jul 9th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$715

7:45pm - 10:29pm
Tue Jul 1st 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

8:30am - 12:49pm
Wed Jul 9th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Tue Jul 1st 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 7 nights

Wed Jul 9th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)
US$715

7:45pm - 10:29pm
Mon Jul 7th 2025

3h 44m
Chicago (ORD) → Calgary (YYC)

Direct

8:30am - 12:49pm
Wed Jul 9th 2025

3h 19m
Calgary (YYC) → Chicago (ORD)

Direct

Mon Jul 7th 2025 United Airlines · UA 1899 Depart at 7:45pm from Chicago (ORD) Fly for 3h 44m Arrive at 10:29pm in Calgary (YYC)

Stay in Calgary for 1 night

Wed Jul 9th 2025 United Airlines · UA 2048 Depart at 8:30am from Calgary (YYC) Fly for 3h 19m Arrive at 12:49pm in Chicago (ORD)

Sarah Belizaire

@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

John Ford

@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

Roaming Sonaa

@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality.

Andy Travels

@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

Travel With Bender

@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Wesley Mergard

@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Flights from Chicago to Calgary (ORD to YYC)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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